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Record Information
Version5.0
StatusExpected but not Quantified
Creation Date2012-09-11 23:12:35 UTC
Update Date2021-09-14 15:45:26 UTC
HMDB IDHMDB0037941
Secondary Accession Numbers
  • HMDB37941
Metabolite Identification
Common NameErgosterol peroxide
DescriptionErgosterol peroxide, also known as 5a,8a-peroxyergosterol, belongs to the class of organic compounds known as ergostane steroids. These are steroids with a structure based on the ergostane skeleton, which arises from the methylation of cholestane at the 24-position. Ergosterol peroxide is an extremely weak basic (essentially neutral) compound (based on its pKa).
Structure
Data?1563863113
Synonyms
ValueSource
(-)-5alpha,8alpha-Epidioxyergosta-6,22-dien-3beta-olHMDB
5a,8a-PeroxyergosterolHMDB
5alpha,8alpha-Epidioxyergosta-6,22-dien-3beta-olHMDB
Ergosterol 5alpha ,8alpha -epidioxideHMDB
Ergosterol endoperoxideHMDB
ERGOSTEROL-5,8-peroxideHMDB
O-(Trifluoromethyl)cinnamic acidHMDB
PeroxyergosterolHMDB
3-Hydroxy-5,7-epidioxyergosta-6,22-dieneMeSH
Ergosterol peroxideMeSH
5,8-Epidioxyergosta-6,22-dien-3-olMeSH
Chemical FormulaC28H44O3
Average Molecular Weight428.6472
Monoisotopic Molecular Weight428.329045274
IUPAC Name5-[(3E)-5,6-dimethylhept-3-en-2-yl]-6,10-dimethyl-16,17-dioxapentacyclo[13.2.2.0¹,⁹.0²,⁶.0¹⁰,¹⁵]nonadec-18-en-13-ol
Traditional Name5-[(3E)-5,6-dimethylhept-3-en-2-yl]-6,10-dimethyl-16,17-dioxapentacyclo[13.2.2.0¹,⁹.0²,⁶.0¹⁰,¹⁵]nonadec-18-en-13-ol
CAS Registry Number2061-64-5
SMILES
CC(C)C(C)\C=C\C(C)C1CCC2C1(C)CCC1C3(C)CCC(O)CC33OOC21C=C3
InChI Identifier
InChI=1S/C28H44O3/c1-18(2)19(3)7-8-20(4)22-9-10-23-25(22,5)13-12-24-26(6)14-11-21(29)17-27(26)15-16-28(23,24)31-30-27/h7-8,15-16,18-24,29H,9-14,17H2,1-6H3/b8-7+
InChI KeyVXOZCESVZIRHCJ-BQYQJAHWSA-N
Chemical Taxonomy
Description Belongs to the class of organic compounds known as ergostane steroids. These are steroids with a structure based on the ergostane skeleton, which arises from the methylation of cholestane at the 24-position.
KingdomOrganic compounds
Super ClassLipids and lipid-like molecules
ClassSteroids and steroid derivatives
Sub ClassErgostane steroids
Direct ParentErgostane steroids
Alternative Parents
Substituents
  • Ergostane-skeleton
  • Ortho-dioxane
  • Cyclic alcohol
  • Dialkyl peroxide
  • Secondary alcohol
  • Oxacycle
  • Organoheterocyclic compound
  • Organic oxygen compound
  • Hydrocarbon derivative
  • Organooxygen compound
  • Alcohol
  • Aliphatic heteropolycyclic compound
Molecular FrameworkAliphatic heteropolycyclic compounds
External DescriptorsNot Available
Ontology
Disposition

Route of exposure:

Biological location:

Source:

Process

Naturally occurring process:

Role

Industrial application:

Biological role:

Physical Properties
StateSolid
Experimental Molecular Properties
PropertyValueReference
Melting Point181.5 - 183 °CNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogPNot AvailableNot Available
Predicted Molecular Properties
PropertyValueSource
Water Solubility2.0e-05 g/LALOGPS
logP6.27ALOGPS
logP6.35ChemAxon
logS-7.3ALOGPS
pKa (Strongest Acidic)15.15ChemAxon
pKa (Strongest Basic)-2.7ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count3ChemAxon
Hydrogen Donor Count1ChemAxon
Polar Surface Area38.69 ŲChemAxon
Rotatable Bond Count4ChemAxon
Refractivity126.82 m³·mol⁻¹ChemAxon
Polarizability51.75 ųChemAxon
Number of Rings5ChemAxon
BioavailabilityYesChemAxon
Rule of FiveNoChemAxon
Ghose FilterNoChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleNoChemAxon
Predicted Spectral Properties

Collision Cross Sections

NameAdductTypeData SourceValueReference
DarkChem[M+H]+PredictedNot Available201.45931661259
DarkChem[M-H]-PredictedNot Available196.01331661259

Retention Indices

Underivatized

Not Available

Derivatized

DerivativeValueReference
Ergosterol peroxide,1TMS,#13436.5251https://arxiv.org/abs/1905.12712
Ergosterol peroxide,1TBDMS,#13663.6367https://arxiv.org/abs/1905.12712
Spectra

GC-MS

Spectrum TypeDescriptionSplash KeyDeposition DateView
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-03di-4139600000-bf51b0c470350fcc4ce82017-09-01View Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (1 TMS) - 70eV, Positivesplash10-0550-6123900000-b90973cd078772a8040c2017-10-06View Spectrum

LC-MS/MS

Spectrum TypeDescriptionSplash KeyDeposition DateView
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-01t9-2003900000-953a700ae3598966539f2016-06-03View Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-01si-9127300000-48fde4c74b50ad587c312016-06-03View Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-001i-9211000000-f87e52d049f1289db4332016-06-03View Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-004i-0000900000-b73c27ef3ea74e4f608d2016-08-03View Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-004i-0000900000-683bc8b3fbffa21c951a2016-08-03View Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-03xr-2109300000-b697bd4f4f99d7ebd8162016-08-03View Spectrum
Biological Properties
Cellular Locations
  • Membrane
Biospecimen LocationsNot Available
Tissue LocationsNot Available
Pathways
Normal Concentrations
Not Available
Abnormal Concentrations
Not Available
Associated Disorders and Diseases
Disease ReferencesNone
Associated OMIM IDsNone
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FooDB IDFDB017110
KNApSAcK IDC00030200
Chemspider ID4528211
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkErgosterol peroxide
METLIN IDNot Available
PubChem Compound5379713
PDB IDNot Available
ChEBI IDNot Available
Food Biomarker OntologyNot Available
VMH IDNot Available
MarkerDB IDNot Available
References
Synthesis ReferenceNot Available
Material Safety Data Sheet (MSDS)Not Available
General References
  1. Dias DA, Urban S: HPLC and NMR studies of phenoxazone alkaloids from Pycnoporus cinnabarinus. Nat Prod Commun. 2009 Apr;4(4):489-98. [PubMed:19475991 ]
  2. Duarte N, Ferreira MJ, Martins M, Viveiros M, Amaral L: Antibacterial activity of ergosterol peroxide against Mycobacterium tuberculosis: dependence upon system and medium employed. Phytother Res. 2007 Jul;21(7):601-4. [PubMed:17357175 ]
  3. Simons K, Toomre D: Lipid rafts and signal transduction. Nat Rev Mol Cell Biol. 2000 Oct;1(1):31-9. [PubMed:11413487 ]
  4. Watson AD: Thematic review series: systems biology approaches to metabolic and cardiovascular disorders. Lipidomics: a global approach to lipid analysis in biological systems. J Lipid Res. 2006 Oct;47(10):2101-11. Epub 2006 Aug 10. [PubMed:16902246 ]
  5. Sethi JK, Vidal-Puig AJ: Thematic review series: adipocyte biology. Adipose tissue function and plasticity orchestrate nutritional adaptation. J Lipid Res. 2007 Jun;48(6):1253-62. Epub 2007 Mar 20. [PubMed:17374880 ]
  6. Lingwood D, Simons K: Lipid rafts as a membrane-organizing principle. Science. 2010 Jan 1;327(5961):46-50. doi: 10.1126/science.1174621. [PubMed:20044567 ]
  7. (). Yannai, Shmuel. (2004) Dictionary of food compounds with CD-ROM: Additives, flavors, and ingredients. Boca Raton: Chapman & Hall/CRC.. .
  8. Gunstone, Frank D., John L. Harwood, and Albert J. Dijkstra (2007). The lipid handbook with CD-ROM. CRC Press.